Benzenesulfonyl chloride → (3-Aminocyclohexyl)(phenylsulfonyl)amine

Participants

Reaction Conditions

Reaction Steps

A solution of 1,3-diaminocyclohexane (1.14 g, 10 mmol, undetermined isomer mixture) in methylene chloride (50 mL) was cooled to 0° C. and phenylsulfonyl chloride (0.64 mL, 5 mmol) was added dropwise. The mixture was stirred at 0° C. for 4 h, then 1N sodium hydroxide solution (10 mL) was added and the mixture stirred an additional 5 min. The phases were separated, the organic phase was dried (K2CO3), filtered, and concentrated in vacuo. Toluene was added and the mixture re-concentrated to remove any remaining diamine, to give 0.77 g of a semi solid. 1H—NMR was consistent with the desired structure. MS (ion spray) 255 (M+1).

Provenance & Evidence